diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index e72c1726f35..1b436bca7d7 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -598,9 +598,13 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 				setShowContextMenu(showMenu)
 
 				if (showMenu) {
-					if (newValue.startsWith("/") && !newValue.includes(" ")) {
-						// Handle slash command - request fresh commands
-						const query = newValue
+					// Extract current line based on cursor position
+					const lineStart = newValue.lastIndexOf("\n", newCursorPosition - 1) + 1
+					const currentLineBefore = newValue.slice(lineStart, newCursorPosition)
+
+					if (currentLineBefore.startsWith("/") && !currentLineBefore.includes(" ")) {
+						// Handle slash command on current line - request fresh commands
+						const query = currentLineBefore
 						setSearchQuery(query)
 						// Set to first selectable item (skip section headers)
 						setSelectedMenuIndex(1) // Section header is at 0, first command is at 1
diff --git a/webview-ui/src/utils/__tests__/context-mentions.spec.ts b/webview-ui/src/utils/__tests__/context-mentions.spec.ts
index 48b03907c34..efc72aa7771 100644
--- a/webview-ui/src/utils/__tests__/context-mentions.spec.ts
+++ b/webview-ui/src/utils/__tests__/context-mentions.spec.ts
@@ -52,7 +52,7 @@ describe("insertMention", () => {
 
 	it("should handle slash command replacement", () => {
 		const result = insertMention("/mode some", 5, "code", true) // Simulating mode selection
-		expect(result.newValue).toBe("code") // Should replace the whole text
+		expect(result.newValue).toBe("code some") // Should replace slash token on current line, preserve rest
 		expect(result.mentionIndex).toBe(0)
 	})
 
@@ -106,18 +106,34 @@ describe("insertMention", () => {
 
 	// --- Tests for isSlashCommand parameter ---
 	describe("isSlashCommand parameter", () => {
-		it("should replace entire text when isSlashCommand is true", () => {
+		it("should replace slash token on current line when isSlashCommand is true", () => {
 			const result = insertMention("/cod", 4, "code", true)
 			expect(result.newValue).toBe("code")
 			expect(result.mentionIndex).toBe(0)
 		})
 
-		it("should replace entire text even when @ mentions exist and isSlashCommand is true", () => {
+		it("should replace slash token but preserve text after cursor when isSlashCommand is true", () => {
 			const result = insertMention("/code @some/file.ts", 5, "debug", true)
-			expect(result.newValue).toBe("debug")
+			expect(result.newValue).toBe("debug @some/file.ts")
 			expect(result.mentionIndex).toBe(0)
 		})
 
+		it("should replace only current line slash token in multiline text", () => {
+			const text = "/code\n/deb"
+			const position = 10 // cursor at end of "/deb"
+			const result = insertMention(text, position, "debug", true)
+			expect(result.newValue).toBe("/code\ndebug")
+			expect(result.mentionIndex).toBe(6) // start of second line
+		})
+
+		it("should preserve other lines when inserting slash command on second line", () => {
+			const text = "/code\nsome text here\n/arc"
+			const position = 25 // cursor at end of "/arc"
+			const result = insertMention(text, position, "architect", true)
+			expect(result.newValue).toBe("/code\nsome text here\narchitect")
+			expect(result.mentionIndex).toBe(21) // start of third line
+		})
+
 		it("should insert @ mention correctly after slash command when isSlashCommand is false", () => {
 			const text = "/code @"
 			const position = 8 // cursor after @
@@ -585,4 +601,29 @@ describe("shouldShowContextMenu", () => {
 		// This case means the regex wouldn't match anyway, but confirms context menu logic
 		expect(shouldShowContextMenu("@/path/with space", 13)).toBe(false) // Cursor after unescaped space
 	})
+
+	// --- Multiline slash command tests ---
+	it("should return true for slash command on second line", () => {
+		const text = "/code\n/deb"
+		const position = 10 // cursor at end of "/deb"
+		expect(shouldShowContextMenu(text, position)).toBe(true)
+	})
+
+	it("should return true for slash command on third line", () => {
+		const text = "/code\nsome text\n/arc"
+		const position = 19 // cursor at end of "/arc"
+		expect(shouldShowContextMenu(text, position)).toBe(true)
+	})
+
+	it("should return false for non-slash text on second line without @", () => {
+		const text = "/code\nhello"
+		const position = 11 // cursor at end of "hello"
+		expect(shouldShowContextMenu(text, position)).toBe(false)
+	})
+
+	it("should return false for slash command with space on second line", () => {
+		const text = "/code\n/debug something"
+		const position = 13 // cursor after space in "/debug "
+		expect(shouldShowContextMenu(text, position)).toBe(false)
+	})
 })
diff --git a/webview-ui/src/utils/context-mentions.ts b/webview-ui/src/utils/context-mentions.ts
index 22dba8864fc..40124212e91 100644
--- a/webview-ui/src/utils/context-mentions.ts
+++ b/webview-ui/src/utils/context-mentions.ts
@@ -32,9 +32,16 @@ export function insertMention(
 ): { newValue: string; mentionIndex: number } {
 	// Handle slash command selection (only when explicitly selecting a slash command)
 	if (isSlashCommand) {
+		const beforeCursor = text.slice(0, position)
+		const afterCursor = text.slice(position)
+		// Find the start of the current line
+		const currentLineStart = beforeCursor.lastIndexOf("\n") + 1
+		const beforeLine = text.slice(0, currentLineStart)
+		// Replace slash command token on the current line (from line start to cursor)
+		const newValue = beforeLine + value + afterCursor
 		return {
-			newValue: value,
-			mentionIndex: 0,
+			newValue,
+			mentionIndex: currentLineStart,
 		}
 	}
 
@@ -367,8 +374,10 @@ export function getContextMenuOptions(
 export function shouldShowContextMenu(text: string, position: number): boolean {
 	const beforeCursor = text.slice(0, position)
 
-	// Check if we're in a slash command context (at the beginning and no space yet)
-	if (text.startsWith("/") && !text.includes(" ") && position <= text.length) {
+	// Check if we're in a slash command context on the current line
+	const currentLineStart = beforeCursor.lastIndexOf("\n") + 1
+	const currentLineBefore = beforeCursor.slice(currentLineStart)
+	if (currentLineBefore.startsWith("/") && !currentLineBefore.includes(" ")) {
 		return true
 	}